Organic Chemistry Study Guide and Solutions
Organic Chemistry Study Guide and Solutions
6th Edition
ISBN: 9781936221868
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
Question
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Chapter 4, Problem 4.59AP
Interpretation Introduction

(a)

Interpretation:

The product X obtained after the acid catalyzed hydration of methylenecyclobutane is to stated.

Concept introduction:

The acid-catalyzed hydration of alkene is the electrophilic addition reaction. The water molecule is added to the alkene resulting in the formation of an alcohol. The more substituted alcohol is the major product.

Interpretation Introduction

(b)

Interpretation:

The structure of the reactive intermediate formed in the rate-limiting step of the reaction is to be stated.

Concept introduction:

The acid-catalyzed hydration of alkene is the electrophilic addition reaction. The water molecule is added to the alkene resulting in the formation of an alcohol. The more substituted alcohol is the major product.

Interpretation Introduction

(c)

Interpretation:

The transition state of the rate-limiting step is to be drawn.

Concept introduction:

Hammond’s postulate states that the structure and energy of the transition state, of a reaction, having intermediate with relatively higher free energy than the reactant and products can be approximated using the structure and energy of intermediate.

Interpretation Introduction

(d)

Interpretation:

The rate limiting step for the dehydration of X is to be stated.

Concept introduction:

The dehydration of alcohol is also done in the presence of the acid as catalyst. This reaction usually requires a higher temperature for the elimination of water molecule from the alcohol.

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6. Consider the following exothermic reaction below. 2Cu2+(aq) +41 (aq)2Cul(s) + 12(aq) a. If Cul is added, there will be a shift left/shift right/no shift (circle one). b. If Cu2+ is added, there will be a shift left/shift right/no shift (circle one). c. If a solution of AgNO3 is added, there will be a shift left/shift right/no shift (circle one). d. If the solvent hexane (C6H14) is added, there will be a shift left/shift right/no shift (circle one). Hint: one of the reaction species is more soluble in hexane than in water. e. If the reaction is cooled, there will be a shift left/shift right/no shift (circle one). f. Which of the changes above will change the equilibrium constant, K?
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